Potassium Hydroxide → 2-Cyclohexylideneacetic acid

HRID 1244452

Reaktionsgleichung

Reaktionsgleichung von HRID 1244452
[OH-].[K+].C([O:5][C:6](=[O:14])[CH:7]=[C:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)C>O.CO>[C:8]1(=[CH:7][C:6]([OH:14])=[O:5])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 73776Ethyl cyclohexylideneacetate

Produkt 1

HCID 962062-Cyclohexylideneacetic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of KOH (1.0 g, 18 mmol) dissolved in water (25 mL) and Intermediate 3 (1.6 g, 9.5 mmol) dissolved in MeOH (5 mL) was stirred for 18 hours at room temperature. The reaction was refluxed for one hour, cooled, then extracted with EtOAc. The aqueous layer was acidified with 1N NCl and extracted with EtOAc, washed with brine, dried (Na2SO4), and concentrated in vacuo to provide 1.3 g (100%) of Intermediate 4. 1H NMR (DMSO-d6) δ: 1.55 (br s, 6H) 2.1 (m, 2H), 2.8 (m, 2H), 5.5 (s, 1H), 11.9 (s, 1H); MS ES−m/e 139.1 (p−1).

Aufarbeitung

  1. temperatureThe reaction was refluxed for one hour
  2. temperaturecooled
  3. extractionextracted with EtOAc
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-965e90e91c0f4179825256b49f9ee004
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07122554B2

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